WO2016021989A1 - Organic electroluminescent compounds and organic electroluminescent devices comprising the same - Google Patents
Organic electroluminescent compounds and organic electroluminescent devices comprising the same Download PDFInfo
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- WO2016021989A1 WO2016021989A1 PCT/KR2015/008307 KR2015008307W WO2016021989A1 WO 2016021989 A1 WO2016021989 A1 WO 2016021989A1 KR 2015008307 W KR2015008307 W KR 2015008307W WO 2016021989 A1 WO2016021989 A1 WO 2016021989A1
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- WIPO (PCT)
- Prior art keywords
- substituted
- group
- unsubstituted
- organic electroluminescent
- alkyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 102
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000005104 aryl silyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000003367 polycyclic group Chemical group 0.000 claims description 11
- 125000001769 aryl amino group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005107 alkyl diaryl silyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000005105 dialkylarylsilyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000005106 triarylsilyl group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 145
- 239000000463 material Substances 0.000 description 66
- 230000032258 transport Effects 0.000 description 37
- 238000002347 injection Methods 0.000 description 30
- 239000007924 injection Substances 0.000 description 30
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 28
- 238000000151 deposition Methods 0.000 description 27
- 239000002019 doping agent Substances 0.000 description 26
- 230000005525 hole transport Effects 0.000 description 20
- 239000012044 organic layer Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- -1 phenylnaphthyl Chemical group 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 6
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 0 *(C(*(c1c(-c2c3)c(cccc4)c4cc1)c2cc1c3-c2ccccc2C11c2ccccc2Oc2c1cccc2)=C(*1)c2ccccc2)c2c1cccc2 Chemical compound *(C(*(c1c(-c2c3)c(cccc4)c4cc1)c2cc1c3-c2ccccc2C11c2ccccc2Oc2c1cccc2)=C(*1)c2ccccc2)c2c1cccc2 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- QQNLHOMPVNTETJ-UHFFFAOYSA-N spiro[fluorene-9,9'-xanthene] Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11C2=CC=CC=C2C2=CC=CC=C21 QQNLHOMPVNTETJ-UHFFFAOYSA-N 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 3
- GJWBRYKOJMOBHH-UHFFFAOYSA-N 9,9-dimethyl-n-[4-(9-phenylcarbazol-3-yl)phenyl]-n-(4-phenylphenyl)fluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C(C=C1)=CC=C1C1=CC=CC=C1 GJWBRYKOJMOBHH-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 229910052761 rare earth metal Inorganic materials 0.000 description 3
- 238000002061 vacuum sublimation Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- OMDTUSYJJFBYMG-UHFFFAOYSA-N 2,4-bis(9,9-dimethylfluoren-2-yl)-6-naphthalen-2-yl-1,3,5-triazine Chemical compound C1=CC=C2C(C)(C)C3=CC(C=4N=C(N=C(N=4)C=4C=C5C=CC=CC5=CC=4)C4=CC=C5C6=CC=CC=C6C(C5=C4)(C)C)=CC=C3C2=C1 OMDTUSYJJFBYMG-UHFFFAOYSA-N 0.000 description 2
- OUGCEPDQCRDITH-UHFFFAOYSA-N C1=C(C=CC2=CC=CC=C12)N1C2=CC=CC=C2C=2C=C(C=CC1=2)C1=CC=C(C=C1)C=1C=CC=2N(C3=CC=CC=C3C=2C=1)C1=CC=CC=C1 Chemical compound C1=C(C=CC2=CC=CC=C12)N1C2=CC=CC=C2C=2C=C(C=CC1=2)C1=CC=C(C=C1)C=1C=CC=2N(C3=CC=CC=C3C=2C=1)C1=CC=CC=C1 OUGCEPDQCRDITH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 238000003775 Density Functional Theory Methods 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- MESMXXUBQDBBSR-UHFFFAOYSA-N n,9-diphenyl-n-[4-[4-(n-(9-phenylcarbazol-3-yl)anilino)phenyl]phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 MESMXXUBQDBBSR-UHFFFAOYSA-N 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 238000004402 ultra-violet photoelectron spectroscopy Methods 0.000 description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- TYBGSZGTQQIASN-UHFFFAOYSA-N 1h-[1]benzofuro[2,3-g]indole Chemical compound C1=CC=C2C3=C(NC=C4)C4=CC=C3OC2=C1 TYBGSZGTQQIASN-UHFFFAOYSA-N 0.000 description 1
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 1
- FXSCJZNMWILAJO-UHFFFAOYSA-N 2-bromo-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(Br)C=C3CC2=C1 FXSCJZNMWILAJO-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- QQTUSVIVKOWUTM-UHFFFAOYSA-N C(C1)C=CC2=C1C(c1ccccc1)NC(c1cccc(-[n](c3ccccc3c3c4)c3cc(C35c6ccccc6Oc6c3cccc6)c4-c3c5cccc3)c1)=N2 Chemical compound C(C1)C=CC2=C1C(c1ccccc1)NC(c1cccc(-[n](c3ccccc3c3c4)c3cc(C35c6ccccc6Oc6c3cccc6)c4-c3c5cccc3)c1)=N2 QQTUSVIVKOWUTM-UHFFFAOYSA-N 0.000 description 1
- BOZLQPTWHYPOQW-UHFFFAOYSA-N C1C=CC(C2N=C(c3cccc4c3cccc4-[n]3c(cc(C4(c5ccccc5-5)c6ccccc6Sc6ccccc46)c-5c4)c4c4ccccc34)N=C(c3ccccc3)N2)=CC1 Chemical compound C1C=CC(C2N=C(c3cccc4c3cccc4-[n]3c(cc(C4(c5ccccc5-5)c6ccccc6Sc6ccccc46)c-5c4)c4c4ccccc34)N=C(c3ccccc3)N2)=CC1 BOZLQPTWHYPOQW-UHFFFAOYSA-N 0.000 description 1
- IUGHTACYPXCYJI-UHFFFAOYSA-N CCC(C1)=C(c2ccccc2)c2ccccc2N=C1c(c1c2cccc1)ccc2-[n]1c(cc(C2(c3c-4cccc3)c3ccccc3Oc3c2cccc3)c-4c2)c2c2c1cccc2 Chemical compound CCC(C1)=C(c2ccccc2)c2ccccc2N=C1c(c1c2cccc1)ccc2-[n]1c(cc(C2(c3c-4cccc3)c3ccccc3Oc3c2cccc3)c-4c2)c2c2c1cccc2 IUGHTACYPXCYJI-UHFFFAOYSA-N 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- 101000687716 Drosophila melanogaster SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 homolog Proteins 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 101000687741 Mus musculus SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 Proteins 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
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- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- DAYQEWXLPJCZLR-UHFFFAOYSA-N c(cc1)ccc1-[n]1c2cc(C(c3ccccc3[N-]3)NC3[n](c(cccc3)c3c3c4)c3cc(C35c6ccccc6Oc6c3cccc6)c4-c3c5cccc3)ccc2c2ccccc12 Chemical compound c(cc1)ccc1-[n]1c2cc(C(c3ccccc3[N-]3)NC3[n](c(cccc3)c3c3c4)c3cc(C35c6ccccc6Oc6c3cccc6)c4-c3c5cccc3)ccc2c2ccccc12 DAYQEWXLPJCZLR-UHFFFAOYSA-N 0.000 description 1
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- ASMWCMPWKWNHTM-UHFFFAOYSA-N c(cc1)ccc1C1=NC(c(cc2)ccc2-[n]2c(cc(C3(c4c-5cccc4)c(cccc4)c4Sc4c3cccc4)c-5c3)c3c3ccccc23)NC(c2c3[o]c(cccc4)c4c3ccc2)N1 Chemical compound c(cc1)ccc1C1=NC(c(cc2)ccc2-[n]2c(cc(C3(c4c-5cccc4)c(cccc4)c4Sc4c3cccc4)c-5c3)c3c3ccccc23)NC(c2c3[o]c(cccc4)c4c3ccc2)N1 ASMWCMPWKWNHTM-UHFFFAOYSA-N 0.000 description 1
- MFOIKNKEUZBQTC-UHFFFAOYSA-N c(cc1)ccc1C1=NC(c2ccccc2)=NC(c(c2ccc3)cccc2c3-[n]2c(cc(C3(c4c-5cccc4)c4ccccc4Oc4c3cccc4)c-5c3)c3c3ccccc23)N1 Chemical compound c(cc1)ccc1C1=NC(c2ccccc2)=NC(c(c2ccc3)cccc2c3-[n]2c(cc(C3(c4c-5cccc4)c4ccccc4Oc4c3cccc4)c-5c3)c3c3ccccc23)N1 MFOIKNKEUZBQTC-UHFFFAOYSA-N 0.000 description 1
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- CRZGVECGYCHFCX-UHFFFAOYSA-N c1ccc(C2N=C(c(cc3)ccc3-[n]3c(cc(C4(c5ccccc5-5)c6ccccc6Sc6ccccc46)c-5c4)c4c4ccccc34)N=C(c3ccccc3)N2)cc1 Chemical compound c1ccc(C2N=C(c(cc3)ccc3-[n]3c(cc(C4(c5ccccc5-5)c6ccccc6Sc6ccccc46)c-5c4)c4c4ccccc34)N=C(c3ccccc3)N2)cc1 CRZGVECGYCHFCX-UHFFFAOYSA-N 0.000 description 1
- SSBHMPDGAXDGRA-UHFFFAOYSA-N c1ccc(C2N=C(c3cc(-c4ccccc4)ccc3)N=C(c(cc3)ccc3-[n](c3ccccc3c3c4)c3cc(C35c6ccccc6Sc6c3cccc6)c4-c3c5cccc3)N2)cc1 Chemical compound c1ccc(C2N=C(c3cc(-c4ccccc4)ccc3)N=C(c(cc3)ccc3-[n](c3ccccc3c3c4)c3cc(C35c6ccccc6Sc6c3cccc6)c4-c3c5cccc3)N2)cc1 SSBHMPDGAXDGRA-UHFFFAOYSA-N 0.000 description 1
- YEABGVKURQPIKL-UHFFFAOYSA-N c1ccc(C2NC([n](c(cccc3)c3c3c4)c3cc(C35c6ccccc6Oc6c3cccc6)c4-c3c5cccc3)=Nc3ccccc23)cc1 Chemical compound c1ccc(C2NC([n](c(cccc3)c3c3c4)c3cc(C35c6ccccc6Oc6c3cccc6)c4-c3c5cccc3)=Nc3ccccc23)cc1 YEABGVKURQPIKL-UHFFFAOYSA-N 0.000 description 1
- WRDUSLKYZLASFR-UHFFFAOYSA-N c1ccc(C2NC([n]3c(cc(C4(c5c-6cccc5)c(cccc5)c5Sc5c4cccc5)c-6c4)c4c4c3cccc4)=[N-]C(c3cccc4c3[o]c3ccccc43)N2)cc1 Chemical compound c1ccc(C2NC([n]3c(cc(C4(c5c-6cccc5)c(cccc5)c5Sc5c4cccc5)c-6c4)c4c4c3cccc4)=[N-]C(c3cccc4c3[o]c3ccccc43)N2)cc1 WRDUSLKYZLASFR-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
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- 238000003618 dip coating Methods 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000002258 gallium Chemical class 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 230000005524 hole trap Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N perylene Chemical compound C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/20—Spiro-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Definitions
- Japanese Patent No. 4947909 presents a blue fluorescent light-emitting device comprising an electron buffer layer, which efficiently injects electrons to a light-emitting layer compared with Alq 3 and controls the movement of electrons, and thereby prevents the reduction of driving voltage and the degradation due to the light-emitting at an interface, and improves the lifespan of the device.
- the organic electroluminescent compound represented by formula 1 will be described in detail as follows.
- “3- to 30-membered heteroaryl(ene)” is an aryl group having at least one, preferably 1 to 4, heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and 3 to 30 ring backbone atoms; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl,
- substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent.
- Substituents of the substituted alkyl group, the substituted aryl group, the substituted heteroaryl group, the substituted cycloalkyl group, the substituted alkoxy group, the substituted trialkylsilyl group, the substituted dialkylarylsilyl group, the substituted alkyldiarylsilyl group, the substituted triarylsilyly group, the substituted mono- or di-alkylamino group, the substituted mono- or di-arylamino group, the substituted alkylarylamino group, and the substituted mono- or polycyclic, alicyclic or aromatic ring in R 1 to R 11 of formula 1 are each independently at least one selected from the group consisting of deuterium; a halogen; a cyan
- the compound of formula 1 may be selected from the group consisting of the following compounds, but is not limited thereto:
- the electron buffer material can be comprised of the organic electroluminescent compound of formula 1 of the present invention alone, or can further include conventional materials generally used in organic electroluminescent materials.
- the compound of formula 1 of the present invention can be included in the light-emitting layer. If included in the light-emitting layer, the compound of formula 1 of the present invention can be contained as a host material, preferably, a phosphorescent host material. Preferably, the light-emitting layer may further comprise at least one dopant, and further comprise compounds other than the compound of formula 1 of the present invention as a second host material, if necessary.
- a first host material (the compound of formula 1) and the second host material may be present in the range of 1:99 to 99:1 in a weight ratio.
- a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
- an electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to a light-emitting medium.
- a hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to a light-emitting medium.
- an oxidative dopant includes various Lewis acids and acceptor compounds; and a reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
- a reductive dopant layer may be employed as a charge generating layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.
- the electron transport layer of the present invention has fast electron current property, and thus Device Examples 4 and 5 provide high efficiency compared with Comparative Example 5.
Abstract
The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By using the organic electroluminescent compound of the present invention, it is possible to produce an organic electroluminescent device having low driving voltage and excellent luminous efficiency such as current efficiency and power efficiency, emitting color of high purity, and having improved lifespan.
Description
The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
Since a double-layered, small molecular, green light-emitting organic electroluminescent device (OLED) was firstly developed by Tang, et al., of Eastman Kodak in 1987, which comprises TPD/Alq3 as a light-emitting layer and a charge transport layer, the development of organic electroluminescent devices has been rapidly achieved, and thus organic electroluminescent devices have currently reached commercialization. At present, an organic electroluminescent device usually uses phosphorescent materials having high luminous efficiency for the realization of panels. In the case of organic electroluminescent devices emitting red or green light, although organic electroluminescent devices using phosphorescent materials have been successfully commercialized, blue light-emitting phosphorescent materials have the following disadvantages: Due to the disappearance of excessive formed excitons, roll-off at high current is reduced thereby resulting in degradation of characteristics; blue light-emitting phosphorescent materials have a problem with respect to long-term storage stability; and color purity is rapidly reduced with the passage of time, and thus it is difficult to realize a full-color display.
Fluorescent light-emitting materials which are currently used also have many problems. First, when they are exposed to a high temperature in the process of the manufacture of panels, current properties may be changed in the organic electroluminescent devices thereby changing the light-emitting luminance, and due to the structural nature, luminance may be reduced according to the reduction in properties of an interface between a light-emitting layer and an electron injection layer. Furthermore, fluorescent light-emitting materials have lower efficiency than phosphorescent light-emitting materials in a material aspect. Although the efficiency improvement was attempted by certain fluorescent light-emitting materials such as the combination of anthracene-based host and pyrene-based dopant, since the materials have a large hole trap, they have a tendency to emit light at the interface with the light-emitting zone in a light-emitting layer being biased toward a hole transport layer. Such light-emitting at the interface not only reduces the lifespan of organic electroluminescent devices but also does not achieve satisfactory efficiency.
The above problems of fluorescent light-emitting materials are no longer possible to be overcome by the mere improvement of materials per se. Thus, attempts are currently being made to change charge movement properties by improving charge transport materials or solve the problems by developing optimized device structures.
Korean Patent Application Laying-open No. 10-2012-0092550 discloses an organic electroluminescent device in which a blocking layer comprising aromatic heterocyclic derivatives having an azine ring is disposed between an electron injection layer and a light-emitting layer.
Japanese Patent No. 4947909 presents a blue fluorescent light-emitting device comprising an electron buffer layer, which efficiently injects electrons to a light-emitting layer compared with Alq3 and controls the movement of electrons, and thereby prevents the reduction of driving voltage and the degradation due to the light-emitting at an interface, and improves the lifespan of the device.
Chinese Patent Application Laying-open No. CN 101870865, and International Publication Nos. WO 2013/149958 A1 and WO 2014/072017 A1 disclose spiro[fluorene-9,9’-xanthene] derivatives.
However, none of the above literature disclose organic electroluminescent compounds in which a benzene ring of the fluorene in the spiro[fluorene-9,9’-xanthene] backbone is fused with benzofuran, benzothiophene, or indole.
The object of the present invention is to provide an organic electroluminescent device having low driving voltage, high luminous efficiency, and long driving lifespan.
The above objective can be achieved by an organic electroluminescent compound represented by the following formula 1:
wherein
W represents O or S;
X represents O, S, or NR11;
R1 to R11 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; and
the heteroaryl group contains at least one hetero atom selected from B, N, O, S, Si, and P.
The organic electroluminescent compound of the present invention can provide an organic electroluminescent device having low driving voltage and high luminous efficiency such as current efficiency and power efficiency, and showing good color purity and improved lifespan.
Hereinafter, the present invention will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
The present invention relates to an organic electroluminescent compound represented by formula 1 and an organic electroluminescent device comprising the same.
The organic electroluminescent compound represented by formula 1 will be described in detail as follows.
Herein, “alkyl” may be specifically exemplified as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. “Cycloalkyl” may be specifically exemplified as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. “3- to 7-membered heterocycloalkyl” is a cycloalkyl having at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and 3 to 7 ring backbone atoms, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. “Aryl(ene)” is a monocyclic or fused ring-based radical derived from an aromatic hydrocarbon; contains spiro compounds in which two rings are linked by one atom, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc. “3- to 30-membered heteroaryl(ene)” is an aryl group having at least one, preferably 1 to 4, heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and 3 to 30 ring backbone atoms; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, pyridopyrimidinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzofuroindole, etc. “Halogen” includes F, Cl, Br, and I.
Herein, “substituted” in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent. Substituents of the substituted alkyl group, the substituted aryl group, the substituted heteroaryl group, the substituted cycloalkyl group, the substituted alkoxy group, the substituted trialkylsilyl group, the substituted dialkylarylsilyl group, the substituted alkyldiarylsilyl group, the substituted triarylsilyly group, the substituted mono- or di-alkylamino group, the substituted mono- or di-arylamino group, the substituted alkylarylamino group, and the substituted mono- or polycyclic, alicyclic or aromatic ring in R1 to R11 of formula 1 are each independently at least one selected from the group consisting of deuterium; a halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; a (C1-C30)alkyl group; a halo(C1-C30)alkyl group; a (C1-C30)alkoxy group; a (C1-C30)alkylthio group; a (C3-C30)cycloalkyl group; a 3- to 7-membered heterocycloalkyl group; a (C6-C30)aryloxy group; a (C6-C30)arylthio group; a 3- to 30-membered heteroaryl group which is unsubstituted or substituted with a (C6-C30)aryl group; a (C6-C30)aryl group which is unsubstituted or substituted with a 3- to 30-membered heteroaryl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; an amino group; a mono- or di-(C1-C30)alkylamino group; a mono- or di-(C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a (C1-C30)alkylcarbonyl group; a (C1-C30)alkoxycarbonyl group; a (C6-C30)arylcarbonyl group; a di(C6-C30)arylboronyl group; a di(C1-C30)alkylboronyl group; a (C1-C30)alkyl(C6-C30)arylboronyl group; a (C6-C30)aryl(C1-C30)alkyl group; and a (C1-C30)alkyl(C6-C30)aryl group; and, preferably, at least one selected from the group consisting of a 5- to 20-membered heteroaryl group; a 5- to 20-membered heteroaryl group which is substituted with a (C6-C18)aryl group; a (C6-C18)aryl group; and a (C6-C18)aryl group which is substituted with a 5- to 20-membered heteroaryl group.
W in formula 1 represents O or S.
X in formula 1 represents O, S, or NR11.
R1 to R11 in formula 1 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur.
Preferably, R1 to R10 each independently represent hydrogen, or a substituted or unsubstituted (C6-C18)aryl group; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (C6-C20) alicyclic or aromatic ring; and, more preferably, hydrogen, or a (C6-C18)aryl group which is unsubstituted or substituted with a (C6-C18)aryl group or a 5- to 20-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C6-C20) aromatic ring which is unsubstituted or substituted with a (C6-C12)aryl group.
Preferably, R11 represents a substituted or unsubstituted (C6-C18)aryl group, or a substituted or unsubstituted 5- to 20-membered heteroaryl group; and more preferably, a (C6-C18)aryl group which is unsubstituted or substituted with a (C6-C18)aryl group or a 5- to 20-membered heteroaryl group, or a 5- to 20-membered heteroaryl group which is unsubstituted or substituted with a (C6-C18)aryl group or a 5- to 20-membered heteroaryl group.
According to one embodiment of the present invention, in formula 1, W represents O or S; X represents O, S, or NR11; R1 to R10 each independently represent hydrogen, or a substituted or unsubstituted (C6-C18)aryl group; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (C6-C20) alicyclic or aromatic ring; and R11 represents a substituted or unsubstituted (C6-C18)aryl group, or a substituted or unsubstituted 5- to 20-membered heteroaryl group.
According to another embodiment of the present invention, in formula 1, W represents O or S; X represents O, S, or NR11; R1 to R10 each independently represent hydrogen, or a (C6-C18)aryl group which is unsubstituted or substituted with a (C6-C18)aryl group or a 5- to 20-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C6-C20) aromatic ring which is unsubstituted or substituted with a (C6-C12)aryl group; and R11 represents a (C6-C18)aryl group which is unsubstituted or substituted with a (C6-C18)aryl group or a 5- to 20-membered heteroaryl group, or a 5- to 20-membered heteroaryl group which is unsubstituted or substituted with a (C6-C18)aryl group or a 5- to 20-membered heteroaryl group.
The compound of formula 1 may be selected from the group consisting of the following compounds, but is not limited thereto:
The organic electroluminescent compound according to the present invention can be prepared by known methods to one skilled in the art, and can be prepared, for example, according to the following reaction scheme 1:
Reaction scheme 1
wherein
W, X, and R1 to R10 are as defined in formula 1; Hal represents a halogen; and n represents 0 or 1.
The present invention further provides an electron buffer material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the electron buffer material.
The electron buffer material can be comprised of the organic electroluminescent compound of formula 1 of the present invention alone, or can further include conventional materials generally used in organic electroluminescent materials.
The organic electroluminescent compound of formula 1 may be used in organic electroluminescent materials other than the electron buffer material. Such organic electroluminescent materials may be preferably a host material, and, more preferably, a phosphorescent host material. If the organic electroluminescent material is used as a host material, it may further include a second host material as described below, in addition to the compound of formula 1.
The organic electroluminescent device according to the present invention may comprise a first electrode, a second electrode, and at least one organic layer between the first and second electrodes, wherein the organic layer comprises at least one compound of formula 1.
One of the first electrode and the second electrode can be an anode and the other can be a cathode. The organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, an electron blocking layer, and an electron buffer layer.
The compound of formula 1 of the present invention can be included in the light-emitting layer. If included in the light-emitting layer, the compound of formula 1 of the present invention can be contained as a host material, preferably, a phosphorescent host material. Preferably, the light-emitting layer may further comprise at least one dopant, and further comprise compounds other than the compound of formula 1 of the present invention as a second host material, if necessary. A first host material (the compound of formula 1) and the second host material may be present in the range of 1:99 to 99:1 in a weight ratio.
The second host material can be any of known phosphorescent host materials and preferably, is selected from the group consisting of the compounds of the following formulae 2 to 6 in view of luminous efficiency:
wherein
Cz represents the following structure:
A represents -O- or -S-;
R21 to R24 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- or 30-membered heteroaryl group, or -SiR25R26R27;
R25 to R27 each independently represent a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group;
L4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 5- or 30-membered heteroarylene group;
M represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- or 30-membered heteroaryl group;
Y1 and Y2 each independently represent -O-, -S-, -N(R31)-, or -C(R32)(R33)-; and Y1 and Y2 are not simultaneously present;
R31 to R33 each independently represent a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- or 30-membered heteroaryl group; and R32 and R33 may be the same or different;
h and i each independently represent an integer of 1 to 3;
j, k, l, and m each independently represent an integer of 0 to 4;
where h, i, j, k, l, or m is an integer of 2 or more, each (Cz-L4), each (Cz), each R21, each R22, each R23, or each R24 may be the same or different.
Specifically, the second host material preferably includes the following:
wherein TPS represents a triphenylsilyl group.
The dopants are preferably one or more phosphorescent dopants. The phosphorescent dopant material applied to the organic electroluminescent device of the present invention is not specifically limited, but preferably may be selected from complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
The dopant included in the organic electroluminescent device of the present invention may be selected from the group consisting of the compounds represented by the following formulae 7 to 9:
wherein
L is selected from the following structures:
R100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group;
R101 to R109 and R111 to R123 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group which is unsubstituted or substituted with halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, a cyano group, or a substituted or unsubstituted (C1-C30)alkoxy group; and R106 to R109 are linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, fluorene which is unsubstituted or substituted with an alkyl group, dibenzothiophene which is unsubstituted or substituted with an alkyl group, or dibenzofuran which is unsubstituted or substituted with an alkyl group; R120 to R123 are linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, quinoline which is unsubstituted or substituted with an alkyl or aryl group;
R124 to R127 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group; R124 to R127 are linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, fluorene which is unsubstituted or substituted with an alkyl group, dibenzothiophene which is unsubstituted or substituted with an alkyl group, or dibenzofuran which is unsubstituted or substituted with an alkyl group;
R201 to R211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl group, or a substituted or unsubstituted (C6-C30)aryl group; R208 to R211 are linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, fluorene which is unsubstituted or substituted with an alkyl group, dibenzothiophene which is unsubstituted or substituted with an alkyl group, or dibenzofuran which is unsubstituted or substituted with an alkyl group;
f and g each independently represent an integer of 1 to 3; where f or g is an integer of 2 or more, each R100 may be the same or different; and
n represents an integer of 1 to 3.
The dopant compound includes the following:
The organic electroluminescent device according to the present invention may comprise a first electrode, a second electrode, and at least one organic layer between the first and second electrodes, wherein the organic layer comprises the materials for an organic electroluminescent device of the present invention.
The organic electroluminescent device of the present invention comprises the organic electroluminescent compound of formula I in an organic layer and may further include at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.
In the organic electroluminescent device of the present invention, an organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides, and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising the metal; or may further comprise at least one of a light-emitting layer and a charge generating layer.
In addition, the organic electroluminescent device of the present invention may emit white light by further comprising at least one light-emitting layer which comprises a blue light-emitting compound, a red light-emitting compound, or a green light-emitting compound which is known in the art, in addition to the compound of the present invention; and may further include a yellow or orange light-emitting layer, if necessary.
Preferably, in the organic electroluminescent device of the present invention, at least one layer (hereinafter, "a surface layer”) selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s). Specifically, it is preferred that a chalcogenide (including oxides) layer of silicon or aluminum is placed on an anode surface of a light-emitting medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer. The surface layer provides operating stability for the organic electroluminescent device. Preferably, the chalcogenide includes SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
Furthermore, preferably, in the organic electroluminescent device of the present invention, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes. In this case, an electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to a light-emitting medium. Furthermore, a hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to a light-emitting medium. Preferably, an oxidative dopant includes various Lewis acids and acceptor compounds; and a reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. A reductive dopant layer may be employed as a charge generating layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.
In order to form each layer constituting the organic electroluminescent device of the present invention, dry film-forming methods, such as vacuum deposition, sputtering, plasma, ion plating methods, etc., or wet film-forming methods, such as spin coating, dip coating, flow coating methods, etc., can be used.
When using a wet film-forming method, a thin film is formed by dissolving or dispersing materials constituting each layer in suitable solvents, such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvents are not specifically limited as long as the materials constituting each layer is soluble or dispersible in the solvents, which do not cause any problems in forming a layer.
Hereinafter, the organic electroluminescent compounds of the present invention, the preparation method thereof, and the properties of devices comprising the compounds will be explained in detail with reference to the representative compounds of the present invention.
Example 1: Preparation of compound A-27
Preparation of compound 1-1
2-Bromofluorene (30.0 g, 115.0 mmol), phenol (109.0 g, 1157.0 mmol), and methanesulfonic acid (30.0 mL) in a reaction vessel were stirred under reflux for 20 hrs. Upon completing the reaction, the mixture was washed with distilled water and the organic layer was extracted with methylene chloride (MC). After drying the extracted organic layer with MgSO4, the solvent was removed by using a rotary evaporator. Thereafter, the obtained product was purified through column chromatography to obtain compound 1-1 (33.6 g, 71 %).
Preparation of compound 1-2
Compound 1-1 (25.0 g, 60.7 mmol), 2-chloroaniline (11.4 g, 91.1 mmol), palladium acetate (0.54 g, 2.43 mmol), tri-tert-butylphosphine (2.4 mL, 4.86 mmol), sodium tert-butoxide (14.6 g, 151.9 mmol), and toluene (180.0 mL) in a reaction vessel were stirred under reflux for 5 hrs. Upon completing the reaction, the mixture was washed with distilled water and the organic layer was extracted with MC. After drying the extracted organic layer with MgSO4, the solvent was removed by using a rotary evaporator. Thereafter, the obtained product was purified through column chromatography to obtain compound 1-2 (16.6 g, 60 %).
Preparation of compound 1-3
Compound 1-2 (16.6 g, 36.2 mmol), palladium acetate (0.81 g, 3.62 mmol), tricyclohexyl phosphonium tetrafluoroborate (2.6 g, 7.24 mmol), cesium carbonate (35.4 g, 108.7 mmol), and dimethylacetamide (200.0 mL) in a reaction vessel were stirred under reflux for 4 hrs. Upon completing the reaction, the mixture was washed with distilled water and the organic layer was extracted with MC. After drying the extracted organic layer with MgSO4, the solvent was removed by using a rotary evaporator. Thereafter, the obtained product was purified through column chromatography to obtain compound 1-3 (11.8 g, 78 %).
Preparation of compound A-27
Compound 1-3 (7.0 g, 16.6 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (7.7 g, 19.9 mmol), palladium acetate (0.37 g, 1.66 mmol), S-phos (1.3 g, 3.32 mmol), sodium tert-butoxide (4.7 g, 49.8 mmol), and xylene (90.0 mL) in a reaction vessel were stirred under reflux for 5 hrs. Upon completing the reaction, the mixture was washed with distilled water and the organic layer was extracted with MC. After drying the extracted organic layer with MgSO4, the solvent was removed by using a rotary evaporator. Thereafter, the obtained product was purified through column chromatography to obtain compound A-27 (9.0 g, 75 %).
Table 1
Comparative Example 1: Production of a blue light-emitting
organic electroluminescent device which does not comprise an electron buffer layer
An OLED device was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (15 Ω/sq) on a glass substrate for an OLED device (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing by sequentially using acetone, ethanol, and distilled water, and was then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus. N4,N4’-diphenyl- N4,N4’-bis(9-pnenyl-9H-carbazol-3-yl)-[1,1’-biphenyl]-4,4’-diamine was introduced into a cell of the vacuum vapor depositing apparatus, and the pressure in the chamber of the apparatus was then controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming the first hole injection layer having a thickness of 60 nm on the ITO substrate. 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN) was then introduced into another cell of the vacuum vapor depositing apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming the second hole injection layer having a thickness of 5 nm on the first hole injection layer. N-([1,1’-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine was introduced into another cell of the vacuum vapor depositing apparatus. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming the first hole transport layer having a thickness of 20 nm on the second hole injection layer. Compound HT-2 was then introduced into another cell of the vacuum vapor depositing apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming the second hole transport layer having a thickness of 5 nm on the first hole transport layer. After forming the hole injection layers and the hole transport layers, a light-emitting layer was then deposited as follows. Compound BH-1 as a host was introduced into one cell of the vacuum vapor depositing apparatus and compound BD-1 as a dopant was introduced into another cell of the apparatus. The two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 2 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 20 nm on the second hole transport layer. Next, 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole as an electron transport material was introduced into one cell of the vacuum vapor depositing apparatus and lithium quinolate was introduced into another cell of the vacuum vapor depositing apparatus. The two materials were evaporated at the same rate and doped in a doping amount of 50 wt%, respectively, to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing lithium quinolate having a thickness of 2 nm as an electron injection layer on the electron transport layer, an Al cathode having a thickness of 80 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10-6 torr prior to use.
The driving voltage at the luminance of 1,000 nit, the luminous efficiency, the CIE color coordinate, and the time taken for the light-emission to be reduced from 100% to 90% at the luminance of 2,000 nit (T90 lifespan) of the OLED device produced as above are provided in Table 2 below.
Device Example 1: Production of a blue light-emitting organic electroluminescent device according to the present invention
An OLED device was produced in the same manner as in Comparative Example 1, except that the thickness of an electron transport layer was reduced to 30 nm, and an electron buffer layer comprising compound A-27 and having a thickness of 5 nm was inserted between the light-emitting layer and the electron transport layer. Evaluation results of the OLED device produced in Device Example 1 are provided in Table 2 below.
Device Example 2: Production of a blue light-emitting organic electroluminescent device according to the present invention
An OLED device was produced in the same manner as in Device Example 1, except that the electron buffer layer was changed to one comprising compound A-133. Evaluation results of the OLED device produced in Device Example 2 are provided in Table 2 below.
Table 2
From Table 2 above, the electron buffer layer of the present invention has fast electron current property, and thus Device Examples 1 and 2 provide high efficiency and long lifespan compared with Comparative Example 1 having no electron buffer layer.
The electron buffer layer can improve the problem that when organic electroluminescent materials are exposed to a high temperature in the process of the manufacture of panels, the current properties of the device may be changed in the devices thereby changing the light-emitting luminance. In order to secure stability at the exposure to a high temperature while having similar current properties compared to those of a device without an electron buffer layer, the properties of compounds included in the electron buffer layer are important. The compound of formula 1 has the structure in which a benzene ring of fluorene in the spiro[fluorene-9,9’-xanthene] backbone is fused to benzofuran, benzothiophene, or indole. In particular, each of the fluorene and the xanthene derivative in the spiro[fluorene-9,9’-xanthene] forms a planar structure, thereby forming a tetra-substituted structure based on the center of a spiro structure, and thus the dihedral angle of the two planes is almost 90° which provides a rectangular form. This effectively modulates π-π stacking interactions via the steric hindrance effect. That is, the compound of formula 1 has excellent morphological stability, and thus has Tg (glass transition temperature) of 172°C which provides very high thermal stability. In this connection, a non-patent literature specifically describes the thermal and oxidation stability of the spiro derivatives (see Macromol. Rapid Commun. 2009, 30, 1745-1750). Furthermore, oxygen as a hetero atom linking to two phenyl rings increases the properties of charge injection and transport, and thus can contribute to fast electron current properties. This may be found in a non-patent literature (see D. Vak et al., Journal of Luminescence, 115 (2005) 109-116). Thus, the compound according to the present invention can greatly contribute to lower driving voltage and improve the lifespan of an organic electroluminescent device. The improvement of properties of devices also has a great effect on guaranteeing stability upon exposure to a high temperature in the process of the manufacture of panels and on improving performance.
In an organic electroluminescent device comprising a first electrode, a second electrode, and a light-emitting layer, electron injection can be controlled by the electron affinity LUMO energy value of an electron buffer layer, by disposing the electron buffer layer between the light-emitting layer and the second electrode.
LUMO (lowest unoccupied molecular orbital) energy value and HOMO (highest occupied molecular orbital) energy value have inherently negative numbers, but the LUMO energy value and the HOMO energy value in the present invention are conveniently expressed as their absolute values. Furthermore, the comparison between LUMO energy values is based on their absolute values. The LUMO energy value and the HOMO energy value in the present invention are calculated by Density Functional Theory (DFT).
In the organic electroluminescent device of the present invention, the LUMO energy value of the electron buffer layer may be larger than the LUMO energy value of the host compounds. A difference between the LUMO energy values of the electron buffer layer and the host compounds may be equal to or less than 0.3 eV. For example, the LUMO energy values of the electron buffer layer and the host compounds may be 1.9 eV and 1.6 eV, respectively. Thus, the difference between the LUMO energy values of the electron buffer layer and the host compounds may be 0.3 eV. The LUMO barrier between the electron buffer layer and the host compounds may be a factor to increase driving voltage. However, since the electron buffer layer comprises the compound of formula 1, it is easier to transport electrons to the host compound compared with other compounds than the compound of formula 1. Therefore, the organic electroluminescent device of the present invention has low driving voltage, high luminous efficiency, and long driving lifespan. In the present invention, the LUMO energy value of the electron buffer layer corresponds to the LUMO energy value of the compound of formula 1 included in the electron buffer layer.
In the organic electroluminescent device of the present invention, an electron transport zone indicates a zone which transports electrons from a second electrode to a light-emitting layer. The electron transport zone may comprise an electron transport compound, a reducing dopant, or the combination thereof. The electron transport compound may be at least one selected from the group consisting of oxazole-, isoxazole-, triazole-, isothiazole-, oxadiazole-, thiadiazole-, perylene-, and anthracene-based compounds, aluminum complexes, and gallium complexes. The reducing dopant may be at least one selected from the group consisting of an alkaline metal, an alkaline metal compound, an alkaline earth metal, a rare-earth metal, a halide thereof, an oxide thereof, and a complex thereof. The electron transport zone may further comprise an electron transport layer, an electron injection layer, or both of them. Each of the electron transport layer and the electron injection layer may be comprised of two or more layers. The LUMO energy value of an electron buffer layer may be smaller or larger than the LUMO energy value of an electron transport zone. For example, the LUMO energy values of the electron buffer layer and the electron transport zone may be 1.9 eV and 1.8 eV, respectively. Thus, the difference between the LUMO energy values of the layer and the zone may be 0.1 eV. Since the electron buffer layer has the LUMO energy value as recited above, it is easy to inject electrons to a light-emitting layer through the electron buffer layer. The LUMO energy value of the electron transport zone may be 1.7 eV or higher, or 1.9 eV or higher.
Specifically, the LUMO energy level of the electron buffer layer may be higher than the LUMO energy levels of the host compound and the electron transport zone. For example, the LUMO energy levels may have the following relationship: the electron buffer layer > the electron transport zone > the host compound. In view of the relationship of the LUMO levels of the respective layers, electrons are restricted between the light-emitting layer and the electron buffer layer, and electron injection is inhibited, and thus the driving voltage can be increased. However, an electron buffer layer comprising the compound of formula 1 easily transports electrons to a light-emitting layer, and thus the organic electroluminescent device of the present invention can have low driving voltage, high luminous efficiency, and long driving lifespan.
LUMO energy values can be easily determined by using various known methods. Conventionally, LUMO energy levels can be determined by using cyclic voltammetry or ultraviolet photoelectron spectroscopy (UPS). Thus, one skilled in the art can easily recognize an electron buffer layer, a host material, and an electron transport zone which satisfy the relationship of the LUMO energy levels of the present invention and practice the present invention. HOMO energy levels can also be easily determined in the same manner as used for the LUMO energy levels.
Device Example 3: Production of an OLED device by using an
organic electroluminescent compound according to the present invention
An OLED device by using an organic electroluminescent compound according to the present invention was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (15 Ω/sq) on a glass substrate for an OLED device (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing by sequentially using trichloroethylene, acetone, ethanol, and distilled water, and was then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus. N4,N4’-diphenyl- N4,N4’-bis(9-phenyl-9H-carbazol-3-yl)-[1,1’-biphenyl]-4,4’-diamine was introduced into a cell of the vacuum vapor depositing apparatus, and the pressure in the chamber of the apparatus was then controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming the first hole injection layer having a thickness of 80 nm on the ITO substrate. 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile was then introduced into another cell of the vacuum vapor depositing apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming the second hole injection layer having a thickness of 3 nm on the first hole injection layer. N-([1,1’-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine was introduced into another cell of the vacuum vapor depositing apparatus. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a hole transport layer having a thickness of 40 nm on the second hole injection layer. After forming the hole injection layers and the hole transport layer, a light-emitting layer was then deposited as follows. Compound A-27 as a host was introduced into one cell of the vacuum vapor depositing apparatus and compound D-1 as a dopant was introduced into another cell of the apparatus. The two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 15 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 40 nm on the hole transport layer. Next, 2,4-bis(9,9-dimethyl-9H-fluorene-2-yl)-6-(naphthalene-2-yl)-1,3,5-triazine and lithium quinolate were evaporated at the rate of 4:6 on another two cells of the vacuum vapor depositing apparatus to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing lithium quinolate having a thickness of 2 nm as an electron injection layer on the electron transport layer, an Al cathode having a thickness of 80 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10-6 torr prior to use.
The produced OLED device showed green emission and had a current density of 2.66 mA/cm2 and a luminance of 1350 cd/m2 at 2.7 V.
Comparative Example 2: Production of an OLED device by using conventional organic electroluminescent compound
An OLED device was produced in the same manner as in Device Example 2, except that compound B-1 was used as a host and compound D-1 was used as a dopant in the light-emitting material, thereby depositing a light-emitting layer having a thickness of 40 nm on the hole transport layer.
The produced OLED device showed green emission and had a current density of 2.59 mA/cm2 and a luminance of 1060 cd/m2 at 4.8 V.
Comparative Example 3: Production of an
OLED
device by using conventional organic
electroluminescent
compound
An OLED device was produced in the same manner as in Device Example 2, except that 4,4’-N,N’-dicarbazol-biphenyl was used as a host and compound D-1 was used as a dopant in the light-emitting material, thereby depositing a light-emitting layer having a thickness of 40 nm on the hole transport layer; aluminum(III) bis(2-methyl-8-quinolinato)-4-phenyl phenolate as a hole blocking layer having a thickness of 10 nm was deposited; and 2,4-bis(9,9-dimethyl-9H-fluorene-2-yl)-6-(naphthalene-2-yl)-1,3,5-triazine and lithium quinolate were evaporated at the rate of 4:6 on another two cells to form an electron transport layer having a thickness of 25 nm on the hole blocking layer.
The produced OLED device showed green emission and had a current density of 4.18 mA/cm2 and a luminance of 1890 cd/m2 at 5.6 V.
Comparative Example 4: Production of an OLED device by using conventional organic electroluminescent compound
An OLED device was produced in the same manner as in Device Example 2, except that compound B-2 was used as a host and compound D-1 was used as a dopant in the light-emitting material, thereby depositing a light-emitting layer having a thickness of 40 nm on the hole transport layer.
The produced OLED device showed green emission and had a current density of 2.39 mA/cm2 and a luminance of 1040 cd/m2 at 3.0 V.
From the above, it can be seen that the organic electroluminescent compound of the present invention has better luminous property than that of conventional materials. Furthermore, the device using the organic electroluminescent compound of the present invention as a host material has excellent luminous property and reduces the driving voltage, thereby increasing the power efficiency and improving the consumption of electric power.
Comparative Example 5: Production of an OLED device by using conventional organic electroluminescent compound
An OLED device was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (15 Ω/sq) on a glass substrate for an OLED device (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing by sequentially using acetone, ethanol, and distilled water, and was then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus. N4,N4’-diphenyl-N4,N4’-bis(9-phenyl-9H-carbazol-3-yl)-[1,1’-biphenyl]-4,4’-diamine was introduced into a cell of the vacuum vapor depositing apparatus, and the pressure in the chamber of the apparatus was then controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming the first hole injection layer having a thickness of 60 nm on the ITO substrate. 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile was then introduced into another cell of the vacuum vapor depositing apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming the second hole injection layer having a thickness of 5 nm on the first hole injection layer. N-([1,1’-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine was introduced into another cell of the vacuum vapor depositing apparatus. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming the first hole transport layer having a thickness of 20 nm on the second hole injection layer. 9-(naphthalene-2-yl)-3-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-carbazole was then introduced into another cell of the vacuum vapor depositing apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming the second hole transport layer having a thickness of 5 nm on the first hole transport layer. After forming the hole injection layers and the hole transport layers, a light-emitting layer was then deposited as follows. Compound BH-1 as a host was introduced into one cell of the vacuum vapor depositing apparatus and compound BD-1 as a dopant was introduced into another cell of the apparatus. The two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 2 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 20 nm on the second hole transport layer. Next, 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (compound ETL-1) as an electron transport material was introduced into one cell of the vacuum vapor depositing apparatus to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing lithium quinolate having a thickness of 2 nm as an electron injection layer on the electron transport layer, an Al cathode having a thickness of 80 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10-6 torr prior to use.
Device Examples 4 and 5: Production of blue light-emitting
organic electroluminescent devices according to the present invention
OLED devices were produced in the same manner as in Comparative Example 5, except that an electron transport material was changed as shown in Table 3 below. Evaluation results of the OLED devices produced in Comparative Example 5, and Device Examples 4 and 5 are provided in Table 3 below.
Table 3
From Table 3 above, the electron transport layer of the present invention has fast electron current property, and thus Device Examples 4 and 5 provide high efficiency compared with Comparative Example 5.
Claims (6)
- An organic electroluminescent compound represented by the following formula 1:
whereinW represents O or S;X represents O, S or NR11;R1 to R11 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; andthe heteroaryl group contains at least one hetero atom selected from B, N, O, S, Si, and P. - The organic electroluminescent compound according to claim 1, wherein the substituents of the substituted alkyl group, the substituted aryl group, the substituted heteroaryl group, the substituted cycloalkyl group, the substituted alkoxy group, the substituted trialkylsilyl group, the substituted dialkylarylsilyl group, the substituted alkyldiarylsilyl group, the substituted triarylsilyl group, the substituted mono- or di-alkylamino group, the substituted mono- or di-arylamino group, the substituted alkylarylamino group, and the substituted mono- or polycyclic, alicyclic or aromatic ring in R1 to R11 each independently are at least one selected from the group consisting of deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a (C1-C30)alkyl, a halo(C1-C30)alkyl, a (C1-C30)alkoxy, a (C1-C30)alkylthio, a (C3-C30)cycloalkyl, a 3- to 7-membered heterocycloalkyl, a (C6-C30)aryloxy, a (C6-C30)arylthio, a 3- to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a (C6-C30)aryl unsubstituted or substituted with a 3- to 30-membered heteroaryl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, an amino, a mono- or di- (C1-C30)alkylamino, a mono- or di- (C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a (C1-C30)alkylcarbonyl, a (C1-C30)alkoxycarbonyl, a (C6-C30)arylcarbonyl, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, and a (C1-C30)alkyl(C6-C30)aryl.
- The organic electroluminescent compound according to claim 1, whereinW represents O or S;X represents O, S or NR11;R1 to R10 each independently represent hydrogen, or a substituted or unsubstituted (C6-C18)aryl group; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic (C6-C20) alicyclic or aromatic ring; andR11 represents a substituted or unsubstituted (C6-C18)aryl group, or a substituted or unsubstituted 5- to 20-membered heteroaryl group.
- The organic electroluminescent compound according to claim 1, whereinW represents O or S;X represents O, S or NR11;R1 to R10 each independently represent hydrogen, or a (C6-C18)aryl unsubstituted or substituted with a (C6-C18)aryl group or a 5- to 20-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic (C6-C20) aromatic ring unsubstituted or substituted with a (C6-C12)aryl group; andR11 represents a (C6-C18)aryl group which is unsubstituted or substituted with a (C6-C18)aryl group or a 5- to 20-membered heteroaryl group, or a 5- to 20-membered heteroaryl group which is unsubstituted or substituted with a (C6-C18)aryl group or a 5- to 20-membered heteroaryl group.
- The organic electroluminescent compound according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
- An organic electroluminescent device comprising the compound according to claim 1.
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| EP15829138.5A EP3177628B1 (en) | 2014-08-08 | 2015-08-07 | Organic electroluminescent compounds and organic electroluminescent devices comprising the same |
| CN201580041551.5A CN106604923B (en) | 2014-08-08 | 2015-08-07 | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
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